Hagerty legal chief acquires 979 shares via plan

Q: Why were HGTY shares withheld on October 1, 2026?

1,076 Class A common shares were withheld for taxes upon vesting of RSUs on October 1, 2026. The RSUs were under an award agreement with a grant date of October 1, 2023.

Q: What was the HGTY ESPP offering period for these shares?

The shares were acquired for the ESPP offering period of April 1, 2026, through September 30, 2026.

The ESPP acquisition price was set at 95% of the issuer's October 1 closing price; separate RSU vesting involved tax withholding.

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Form Type

Rhea-AI Filing Summary

Hagerty, Inc. Chief Legal Officer Diana Chafey acquired 979 Class A common shares through the Employee Stock Purchase Plan on October 2, 2026, at $12.79 per share; the price equaled 95% of the October 1, 2026 closing price. On October 1, 2026, 1,076 shares were withheld for taxes upon vesting of RSUs under an award agreement with a grant date of October 1, 2023. No Rule 10b5-1 plan is reported.

Insider Trade Summary

2 transactions reported

Mixed 2 txns

Insider Chafey Diana

Role Chief Legal Officer

Type	Security	Shares	Price	Value
Grant/Award	Class A Common Stock ^{F2, F3}	979	$12.79	$13K
Tax Withholding	Class A Common Stock ^F1	1,076	$13.46	$14K

Holdings After Transaction: Class A Common Stock — 76,911 shares (Direct)

Footnotes (3)

F1. Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of RSUs pursuant to Reporting Person's RSU award agreement with a grant date of October 1, 2023.
F2. Shares acquired pursuant to the Hagerty, Inc. Employee Stock Purchase Plan ("ESPP") for the ESPP offering period of April 1, 2026 through September 30, 2026.
F3. In accordance with the ESPP, the per share price paid for these shares was an amount equal to 95% of the closing price of the Issuer's stock on October 1, 2026.

Key Figures

ESPP acquisition: 979 shares ESPP price per share: $12.79 per share ESPP price formula: 95% +3 more

6 metrics

ESPP acquisition 979 shares October 2, 2026

ESPP price per share $12.79 per share 95% of the closing price on October 1, 2026

ESPP price formula 95% Of the issuer's closing price on October 1, 2026

Shares withheld for taxes 1,076 shares Upon RSU vesting on October 1, 2026

Reported price per share for tax withholding $13.46 per share October 1, 2026

RSU award grant date October 1, 2023 Grant date stated in the award agreement footnote

Key Terms

Employee Stock Purchase Plan ("ESPP"), RSU award agreement, vesting of RSUs

3 terms

Employee Stock Purchase Plan ("ESPP") financial

"acquired pursuant to the Hagerty, Inc. Employee Stock Purchase Plan"

RSU award agreement financial

"pursuant to Reporting Person's RSU award agreement"

A RSU award agreement is a legal contract that grants restricted stock units — promises of company stock to an employee or advisor — and spells out how many units are granted, when they become actual shares (vesting), and any conditions or tax rules. Investors care because these agreements create future share issuance and compensation cost, which can dilute existing holders and signal how the company rewards and retains key people, much like a delayed paycheck paid in stock.

vesting of RSUs financial

"withheld for taxes upon vesting of RSUs"

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

How many shares did HGTY Chief Legal Officer Diana Chafey acquire?

Diana Chafey, Hagerty, Inc.'s Chief Legal Officer, acquired 979 Class A common shares through the Employee Stock Purchase Plan on October 2, 2026, at $12.79 per share. The price equaled 95% of the issuer's closing price on October 1, 2026. No Rule 10b5-1 plan is reported.

Why were HGTY shares withheld on October 1, 2026?

1,076 Class A common shares were withheld for taxes upon vesting of RSUs on October 1, 2026. The RSUs were under an award agreement with a grant date of October 1, 2023.

What was the HGTY ESPP offering period for these shares?

The shares were acquired for the ESPP offering period of April 1, 2026, through September 30, 2026.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Available on EDGAR 10/05/2026 - 05:15 PM Accepted by SEC EDGAR 10/05/2026 - 05:15 PM

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Chafey Diana

(Last)

(First)

(Middle)

121 DRIVERS EDGE

(Street)

TRAVERSE CITY

MICHIGAN

49684

(City)

(State)

(Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
Hagerty, Inc. [ HGTY ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director	10% Owner
X	Officer (give title below)	Other (specify below)
	Chief Legal Officer

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
10/01/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Class A Common Stock	10/01/2026		F		1,076⁽¹⁾	D	$13.46	75,932	D
Class A Common Stock	10/02/2026		A		979⁽²⁾	A	$12.79⁽³⁾	76,911	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)

Explanation of Responses:

1. Represents total number of shares of Class A Common Stock of the Issuer withheld for taxes upon vesting of RSUs pursuant to Reporting Person's RSU award agreement with a grant date of October 1, 2023.

2. Shares acquired pursuant to the Hagerty, Inc. Employee Stock Purchase Plan ("ESPP") for the ESPP offering period of April 1, 2026 through September 30, 2026.

3. In accordance with the ESPP, the per share price paid for these shares was an amount equal to 95% of the closing price of the Issuer's stock on October 1, 2026.

Remarks:

	/s/ Rebecca Patel, Power of Attorney	10/05/2026
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR